In his book Digital Trailblazer, Isaac Sacolick shares his lessons learned as a CIO and CTO about how to succeed in the C-suite in the age of digital transformation. In his first-person narrative, Sacolick shares personal stories from tense IT Ops conference calls to make-or-break executive meetings. Sacolick presents the challenging scenarios faced by product, technology, and data leaders and helps listeners learn to lead transformations and become what he’s termed “Digital Trailblazers.”

Isaac is a successful CIO who has led digital transformation, product development, innovation, agile management and data science programs in multiple organizations. Today, Isaac is the President of StarCIO, a company he founded that guides organizations on digital transformation and enables agile, DevOps, data and product management practices.

In this interview, we discuss why he chose to write Digital Trailblazer, who he hopes reads the book, what defines digital transformation success and how to overcome associated hurdles within organizations. The conversation shared is edited for brevity.

Thank you for taking the time today, Isaac. Perhaps you can start by sharing about yourself and why you wrote this book.

Well, I’ve written two books. The first book was Driving Digital, which came out in 2017. It was the culmination of two careers I had. My career comprised about 20 years, of which ten were CIO and ten years as CTO. And in 2007, while a CIO, I was charged with transformation before “digital transformation” became a buzzword.

I worked at companies already facing some of the early impacts of digital disruption. They hired me to come in and figure out how to do software development effectively. They wanted to improve their experiences, build new products, and essentially act like a startup. They wanted to be data-driven. However, they realized they couldn’t afford the same types of talent and technologies that SaaS companies could. I did that three times at three companies—one company in media, one in construction, and one in financial services.

My first book, Driving Digital, talks about how to scale agile or run agile mindsets and cultures and how to implement DevOps in traditional organizations. It explains what being data-driven is all about and how to improve product development with product management. It talks about how to change the culture. Driving Digital is essentially a playbook for these areas.

After publishing the book in 2017, I met many people through the speaking engagements and workshops I led. The most interesting people I met were those aspiring to lead transformation programs. These were product managers, DevOps engineers, agile leaders, data scientists and many others in operations and security. People understood what it took to participate in transformation initiatives in their disciplines, but they didn’t have the broad experience to lead cross-disciplinary programs. They didn’t understand how to sell their ideas and change people’s mindsets beyond how things work today.

What’s Digital Trailblazer all about, and who is the target readership?

Instead of writing another playbook, I wrote a book about my experiences. It reads like a novel. You’re sitting next to me as I’m dealing with bugs, answering technical questions at a board meeting, and handling detractors trying to build a product out. There are ten chapters in Digital Trailblazer, and each chapter ends with five important lessons learned.

I wrote it for two audiences. The first audience is C-levels because C-level executives need to spend more of their time business-focused, learning customers, learning markets, and partnering with their executives on how to transform the business every few years. I believe transformation is a two-to-three-year cycle. What we plan for right now for the next two years will evolve. And then there will be new technologies and capabilities, and our competitors will be doing different things. There’ll be new disruptions that we can’t anticipate right now. We will then have to transform again. That’s where the C-suite has to focus. Therefore, they need their lieutenants to handle more of the day-to-day transformation work, whether it’s DevOps or it is becoming data-driven.

The second audience is aspiring transformation leaders who want to build confidence to lead larger initiatives and take on bigger roles. Some aspire to be CIOs, CDOs and CTOs one day. How can these Digital Trailblazers build their knowledge and confidence?

I admire Digital Trailblazers and know their challenges. Out of grad school, I had to learn many things on my own as I became a CTO in my 20s. Today’s new CTOs are going through similar challenges because of how quickly they’re being asked to take leadership roles. The feedback I get is that the stories I shared help them understand how to think about their jobs differently.

Here’s one example. I’m sitting there one day as a newly hired CIO, and the head of product comes to me and asks, What’s your roadmap?” Every IT professional hears that somewhere in their journey. What’s your roadmap? I tell the story about how I answered that question. There were some good things about how I answered the question, and there are ways I could have handled things better. I share these stories in Digital Trailblazer.

There are places where I’ve shared some wins, but many stories are like Holy Crap!

What defines transformational success? What ingredients need to be there to have a successful digital transformation?

I think that goes back to what the business objectives are. There are a few things that are fairly common to look at. Growth is probably the first thing to consider, especially in targeted markets and areas in which you’re trying to expand.

Going back to my days in the media business. We were transforming content, subscription business, and advertisement models from print to digital. It’s easy to visualize that in retail, such as when a store experience is shifted to digital experiences. In the next ten years, that will be Metaverse experiences. Also, in business-to-consumer, it’s easy to see because we’ve witnessed a transformation in Uber and Airbnb.

But you’re also starting to see it in more traditional industries. I’ve done a lot of work with hospitals over the last year. Take telehealth. Telehealth has gone from a very low percentage of experiences to becoming a norm. Over the next five years, as more hospitals open their ability to take mobile data gathered on phones, how do they change the experiences they provide to athletes versus people who need acute care?

I get the sense that technology plays a small, albeit important, role in the challenges within digital transformation efforts. What are some of the pitfalls CIOs typically encounter when trying to bring the company’s vision for change alive within an organization? 

I always explain transformation through a process, people and technology lens. Consider process. If you’re stalled doing waterfall processes or your data is still being exported from on-prem databases into Excel spreadsheets, you have a process problem. How do I change the way people work? That’s going to bring up a leadership and people-talent issue.

How do I execute the strategy? How do I get more people to lead and deliver transformation programs, not just technology? And technology becomes important because when you start shopping and looking at the kind of experiences you need. You need to also look at what type of integration you require. What’s the scale you require? What are the compliance issues? If you look at any single category of technology you need, you’ll have hundreds of options to choose from, and you’re not going to spend six months building a mile-long spreadsheet of every feature to compare everything.

So how do you run efficient POCs around these and then scale the working technologies?

Returning to your first question, where people make mistakes is not thinking top-down, and then only executing top-down. Top-down answers questions like, “What’s the strategy from a business perspective? What are we trying to transform? What businesses are we trying to get into?” It’s really important to set some north poles and define a vision to succeed.

But most transformation work starts bottom up. Consider product management. One of the most challenging areas for non-technology companies is transitioning from project management or sales-driven mindsets to having somebody run a product. This is true whether it’s an internal or external-facing product.

Is that because getting buy-in for change is tough, as people tend to be naturally resistant to change?

I talked about that in Digital Trailblazer. The first part of the transformation is trying to find the internal early adopters. The ones that are excited by doing things differently. Excited by the technology. They may be in their fourth or fifth line of a deep product portfolio and are eager to find ways to move transformation forward faster. Those are going to be your early adopters.

But how do you bring more people onto your transformational ship when you start getting into it? You’re going to get folks in the organization that are incentivized differently. Their incentives are based on the old way that business was operating. So how do you have the CEO and HR talk about how they will change the incentive programs? That’s a very top-down view.

If you take a bottom-up view, part of what you’re going to do is to bring automation. That’s where you’re going to see efficiencies. You will take something that’s very labor-intensive and more scalable or take something that’s very error-prone and improve quality. You’re going to bring automation, but if I use that word — automation —the CFO will think you’re going to be cutting staff. But that’s not the reality.

It’s nearly impossible to fully automate and not need people anymore.

You can probably automate 80% of any operation fairly easily, but every percent higher after that gets more complicated and expensive. When it comes to automation, you have to set very different expectations. And when staff hear the word automation, they wonder how this impacts them. They want to know what they are going to be doing differently. And so, in digital transformation, you have to project where the jobs will be. You have to project what people will do beyond what they do today and what the transformation impacts. What’s the new organizational model going to look like? What are people doing differently? How am I going to get people excited by that?

And this cycle of transformation is going to be continuous. We will be continuously transforming our organizations and the jobs people have in the organization.